A concise and divergent approach to radicamine B and hyacinthacine A₃ based on a step-economic transformation

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• 作者：Jin-Cheng Liao ; Kai-Jiong Xiao ; Xiao Zheng ; Pei-Qiang Huang ; ^{pqhuang@xmu.edu.cn}
• 关键词：Step-economy ; Azasugars ; Alkaloids ; Glycosidase inhibitors ; Hantzsch ester
• 刊名：Tetrahedron
• 出版年：2012
• 期刊代码：107_00404020
• 类别：ch
• 出版时间：1 July, 2012
• 卷：68
• 期：26
• 页码：5297-5302
• 文件大小：694 K

摘要

Based on our recently developed step-economic methodology of reductive alkylation of lactams/amides, we have developed a two-step synthesis of azasugar radicamine B (2a) and a four-step synthesis of azasugar hyacinthacine A₃ (5) from the common chiral building block 12. Hantzsch ester (HEH) was used as a milder hydride donor in the one-pot stereoselective reductive alkylation of lactam 12. The Wacker oxidation of fully substituted pyrrolidine derivative 2,5-trans-17 led to the synthesis of hyacinthacine A₃ (5). Compound 2,5-trans-17 could also serve as a plausible key intermediate for the synthesis of broussonetine sub-class of azasugars.